Skip to main content
Log in

Synthesis of New α-Aminophosphonates Based on Cyclohexylamine

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

A series of new α-aminophosphonates was synthesized based on the acid-catalyzed Kabachnik–Fields reaction involving diethyl phosphite, cyclohexylamine and substituted benzaldehyde. Structure of the reaction products was established by IR, NMR spectroscopy, and mass spectrometry methods.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme

REFERENCES

  1. Mucha, A., Kafarski, P., and Berlicki, Ł., J. Med. Chem., 2011, vol. 54, p. 5955. https://doi.org/10.1021/jm200587f

    Article  CAS  PubMed  Google Scholar 

  2. Seto, H., Kuzuyama, T., Seto, H., and Kuzuyama, T., Nat. Prod. Rep., 1999, vol. 16, p. 589. https://doi.org/10.1039/a809398i

    Article  CAS  PubMed  Google Scholar 

  3. Fields, S.C., Tetrahedron, 1999, vol. 55, p. 12237. https://doi.org/10.1016/S0040-4020(99)00701-2

    Article  CAS  Google Scholar 

  4. Romanowska, J., Kolodziej, K., Sobkowski, M., Rachwalak, M., Jakubowski, T., Golebiewska, J., Kraszewski, A., Boryski, J., Dabrowska, A., and Stawinski, J., Eur. J. Med. Chem., 2019, vol. 164, p. 47. https://doi.org/10.1016/j.ejmech.2018.12.038

    Article  CAS  PubMed  Google Scholar 

  5. Wang, Q., Zhu, M., Zhu, R., Lu, L., Yuan, C., Xing, S., Fu, X., Mei, Y., and Hang, Q., Eur. J. Med. Chem., 2012, vol. 49, p. 354. https://doi.org/10.1016/j.ejmech.2012.01.03

    Article  CAS  PubMed  Google Scholar 

  6. Romero-Estudillo, I., Viveros-Ceballos, J.L., CazaresCarreño, O., González-Morales, A., de Jesús, B.F., López-Castillo, M., Razo-Hernández, R.S., CastañedaCorral, G., and Ordóñez, M., Bioorg. Med. Chem., 2019, vol. 27, p. 2376. https://doi.org/10.1016/j.bmc.2018.12.041

    Article  CAS  PubMed  Google Scholar 

  7. Pudovik, A.N., Doklady Akad. Nauk SSSR, 1952, vol. 83, p. 865.

    CAS  Google Scholar 

  8. Alfonsov, V.A., Phosphorus, Sulfur, Silicon, Relat. Elem., 2008, vol. 183, p. 2637. https://doi.org/10.1080/10426500802344022

    Article  CAS  Google Scholar 

  9. Zhao, D., Mao, L., Yang, D., and Wang, R., J. Org. Chem., 2010, vol. 75, p. 6756. https://doi.org/10.1021/jo1014917

    Article  CAS  PubMed  Google Scholar 

  10. Jemal, A., Bray, F., Center, M.M., Ferlay, J., Ward, E., and Forman, D., C. A. Cancer J. Clin., 2011, vol. 61, p. 69. https://doi.org/10.3322/caac.20107

    Article  Google Scholar 

  11. Cherkasov, R.A. and Galkin, V.I., Russ. Chem. Rev., 1998, vol. 67, p. 857. https://doi.org/10.1070/RC1998v067n10ABEH000421

    Article  Google Scholar 

  12. Fields, E.K., J. Am. Chem. Soc., 1952, vol. 74, p. 1528. https://doi.org/10.1021/ja01126a054

    Article  CAS  Google Scholar 

  13. Zefirov, N.S. and Matveeva, E.D., Arkivoc, 2008, vol. 1, p. 1. https://doi.org/10.3998/ark.5550190.0009.101

    Article  Google Scholar 

  14. Kaboudin, B., Arefi, M., Emadi, S., and Sheikh-Hasani, V., Bioorg. Chem., 2012, vol. 41, p. 22. https://doi.org/10.1016/j.bioorg.2012.01.003

    Article  CAS  PubMed  Google Scholar 

  15. Kaboudin, B., Emadi, S., Faghihi, M.R., Fallahi, M., and Sheikh-Hasani, V., J. Enzyme Inhib. Med. Chem., 2013, vol. 28, p. 576. https://doi.org/10.3109/14756366.2012.663362

    Article  CAS  PubMed  Google Scholar 

  16. Jiang, G., Madan, D., and Prestwich, G.D., Bioorg. Med. Chem. Lett., 2011, vol. 21, p. 5098. https://doi.org/10.1016/j.bmcl.2011.03.068

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. Kim, I.-H., Park, Y.-K., Nishiwaki, H., Hammock, B.D., and Nishi, K., Bioorg. Med. Chem., 2015, vol. 23, p. 7199. https://doi.org/10.1016/j.bmc.2015.10.016

    Article  CAS  PubMed  Google Scholar 

  18. Drąg, M., Grembecka, J., Pawełczak, M., and Kafarski, P., Eur. J. Med. Chem., 2005, vol. 40, p. 764. https://doi.org/10.1016/j.ejmech.2005.02.011

    Article  CAS  PubMed  Google Scholar 

  19. Węglarz-Tomczak, E., Berlicki, Ł., Pawełczak, M., Nocek, B., Joachimiak, A., and Mucha, A., Eur. J. Med. Chem., 2016, vol. 117, p. 187. https://doi.org/10.1016/j.ejmech.2016.04.018

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. Shi, L., Huang, X.-F., Zhu, Z.-W., Li, H.-Q., Xue, J.-Y., Zhu, H.-L., and Liu, C.-H., Aust. J. Chem., 2008, vol. 61, p. 472. https://doi.org/10.1071/CH08029

    Article  CAS  Google Scholar 

  21. Abdou, W.M. and Bekheit, M.S., Arab. J. Chem., 2018, vol. 11, p. 1260. https://doi.org/10.1016/j.arabjc.2015.04.014

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

The authors are grateful to the Collective Spectroanalytical Center for Physicochemical Studies of the Structure and Properties of the Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences” for the technical support of the studies.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. V. Smolobochkin.

Ethics declarations

No conflict of interest was declared by the authors.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Smolobochkin, A.V., Gazizov, A.S., Doszhanova, K.A. et al. Synthesis of New α-Aminophosphonates Based on Cyclohexylamine. Russ J Gen Chem 90, 1100–1103 (2020). https://doi.org/10.1134/S1070363220060274

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363220060274

Keywords:

Navigation